ES2215161T3 - Diastereoisomero del ester 1-(isopropoxicarboniloxi)-etilico del acido 3-cefem-4-carboxilico y procedimiento para su preparacion. - Google Patents
Diastereoisomero del ester 1-(isopropoxicarboniloxi)-etilico del acido 3-cefem-4-carboxilico y procedimiento para su preparacion.Info
- Publication number
- ES2215161T3 ES2215161T3 ES92114982T ES92114982T ES2215161T3 ES 2215161 T3 ES2215161 T3 ES 2215161T3 ES 92114982 T ES92114982 T ES 92114982T ES 92114982 T ES92114982 T ES 92114982T ES 2215161 T3 ES2215161 T3 ES 2215161T3
- Authority
- ES
- Spain
- Prior art keywords
- acid
- formula
- diastereoisomer
- pure
- diastereoisomers
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000002253 acid Substances 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims description 10
- 239000000203 mixture Substances 0.000 claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 238000001914 filtration Methods 0.000 claims abstract description 11
- 238000002425 crystallisation Methods 0.000 claims abstract description 4
- 230000008025 crystallization Effects 0.000 claims abstract description 4
- -1 1- (Isopropoxycarbonyloxy) -ethyl Chemical group 0.000 claims description 40
- 150000002148 esters Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 5
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 5
- 150000001449 anionic compounds Chemical class 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 3
- 229910001412 inorganic anion Inorganic materials 0.000 claims description 3
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 3
- BRIXOPDYGQCZFO-UHFFFAOYSA-N 4-ethylphenylsulfonic acid Chemical compound CCC1=CC=C(S(O)(=O)=O)C=C1 BRIXOPDYGQCZFO-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 235000011149 sulphuric acid Nutrition 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 67
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- LTINZAODLRIQIX-FBXRGJNPSA-N cefpodoxime proxetil Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC)C(=O)OC(C)OC(=O)OC(C)C)C(=O)C(=N/OC)\C1=CSC(N)=N1 LTINZAODLRIQIX-FBXRGJNPSA-N 0.000 description 6
- 229960004797 cefpodoxime proxetil Drugs 0.000 description 6
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 6
- 239000003242 anti bacterial agent Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- WYUSVOMTXWRGEK-HBWVYFAYSA-N cefpodoxime Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC)C(O)=O)C(=O)C(=N/OC)\C1=CSC(N)=N1 WYUSVOMTXWRGEK-HBWVYFAYSA-N 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229940088710 antibiotic agent Drugs 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- ZWNCJCPLPUBNCZ-UHFFFAOYSA-N 1,2-dimethoxyethane;hydrate Chemical compound O.COCCOC ZWNCJCPLPUBNCZ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052681 coesite Inorganic materials 0.000 description 3
- 229910052906 cristobalite Inorganic materials 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 229940002612 prodrug Drugs 0.000 description 3
- 239000000651 prodrug Substances 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 229910052682 stishovite Inorganic materials 0.000 description 3
- 229910052905 tridymite Inorganic materials 0.000 description 3
- XZVBIIRIWFZJOE-UHFFFAOYSA-N 1-iodoethyl propan-2-yl carbonate Chemical compound CC(C)OC(=O)OC(C)I XZVBIIRIWFZJOE-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 229930186147 Cephalosporin Natural products 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229940124587 cephalosporin Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- KNNUUKGCYYHKDF-JHXJAOOTSA-N 1-acetyloxyethyl (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-[(z)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)\C=C/C)C(=O)OC(C)OC(C)=O)C(=O)C(=N/O)\C1=CSC(N)=N1 KNNUUKGCYYHKDF-JHXJAOOTSA-N 0.000 description 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
- RIOSJKSGNLGONI-UHFFFAOYSA-N 2-phenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 RIOSJKSGNLGONI-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- KEJCWVGMRLCZQQ-YJBYXUATSA-N Cefuroxime axetil Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(=O)OC(C)OC(C)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 KEJCWVGMRLCZQQ-YJBYXUATSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000252095 Congridae Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229910004039 HBF4 Inorganic materials 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- FXTTXRHGRZVUAG-UHFFFAOYSA-N P.Cl.Cl.Cl.Cl.Cl Chemical compound P.Cl.Cl.Cl.Cl.Cl FXTTXRHGRZVUAG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 108010073038 Penicillin Amidase Proteins 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229960002620 cefuroxime axetil Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4129771 | 1991-09-07 | ||
| DE4129771 | 1991-09-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2215161T3 true ES2215161T3 (es) | 2004-10-01 |
Family
ID=6440090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES92114982T Expired - Lifetime ES2215161T3 (es) | 1991-09-07 | 1992-09-02 | Diastereoisomero del ester 1-(isopropoxicarboniloxi)-etilico del acido 3-cefem-4-carboxilico y procedimiento para su preparacion. |
Country Status (30)
| Country | Link |
|---|---|
| US (3) | US5461043A (cs) |
| EP (1) | EP0531875B1 (cs) |
| JP (1) | JP2667943B2 (cs) |
| KR (1) | KR100239253B1 (cs) |
| CN (1) | CN1040002C (cs) |
| AT (1) | ATE262533T1 (cs) |
| AU (1) | AU647307B2 (cs) |
| BR (1) | BR9203464A (cs) |
| CA (1) | CA2077562C (cs) |
| CZ (1) | CZ282320B6 (cs) |
| DE (1) | DE59209994D1 (cs) |
| DK (1) | DK0531875T3 (cs) |
| EG (1) | EG20237A (cs) |
| ES (1) | ES2215161T3 (cs) |
| FI (1) | FI108725B (cs) |
| HR (1) | HRP920310A2 (cs) |
| HU (1) | HU219588B (cs) |
| IL (1) | IL103064A (cs) |
| MA (1) | MA22646A1 (cs) |
| MX (1) | MX9205081A (cs) |
| NO (1) | NO302122B1 (cs) |
| NZ (1) | NZ244224A (cs) |
| PH (1) | PH30743A (cs) |
| PL (1) | PL171644B1 (cs) |
| PT (1) | PT531875E (cs) |
| RS (1) | RS49877B (cs) |
| RU (1) | RU2075480C1 (cs) |
| SI (1) | SI9200204B (cs) |
| SK (1) | SK279013B6 (cs) |
| ZA (1) | ZA926710B (cs) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL99898A (en) * | 1990-11-09 | 1996-10-31 | Eisai Co Ltd | 7-Acyl-3-substituted carbamoyloxy cephem compounds their preparation and antibacterial compositions containing them |
| ATE262533T1 (de) * | 1991-09-07 | 2004-04-15 | Aventis Pharma Gmbh | Diastereomer des 3-cephem-4-carbonsäure-1-(- isopropoxycarbonyloxy)ethylesters und verfahren zu dessen herstellung |
| TW212181B (cs) * | 1992-02-14 | 1993-09-01 | Hoechst Ag | |
| EP0570849B1 (de) * | 1992-05-21 | 1998-03-25 | Hoechst Aktiengesellschaft | Verfahren zur Spaltung von Cephalosporin Prodrugestern zu 7-Amino-3-methoxymethylceph-3-em-4-carbonsäure |
| US5817351A (en) * | 1995-04-07 | 1998-10-06 | Abbott Laboratories | Calcium fortified low pH beverage |
| US5928691A (en) * | 1997-05-01 | 1999-07-27 | Nestec S.A. | Calcium complex and a process of making a food fortified with calcium |
| US6024994A (en) * | 1997-11-06 | 2000-02-15 | Nestec S.A. | Calcium complexes for fortification of foods and process of making |
| AT413383B (de) | 1998-01-09 | 2006-02-15 | Sandoz Ag | Verfahren zur isolierung eines diastereoisomerengemisches von cefpodoxim proxetil |
| US6036985A (en) * | 1998-04-03 | 2000-03-14 | Nestec S.A. | Calcium complex and food fortified therewith |
| US6039986A (en) * | 1998-07-10 | 2000-03-21 | Nestec S.A. | Fortification of foodstuff |
| AT408226B (de) * | 1999-05-05 | 2001-09-25 | Biochemie Gmbh | Kristalliner 7-(2-(2-formylaminothiazol-4-yl)-2 |
| HK1044761A1 (zh) * | 1999-05-07 | 2002-11-01 | Ranbaxy Laboratories, Limited | 制备头孢泊肟酸的方法 |
| IN191496B (cs) * | 1999-07-30 | 2003-12-06 | Ranbaxy Lab Ltd | |
| KR100342944B1 (ko) * | 1999-11-08 | 2002-07-02 | 민경윤 | 고순도 세프포독심 프록세틸의 제조방법 |
| US6740344B2 (en) * | 2000-12-01 | 2004-05-25 | General Mill, Inc. | Calcium fortified products and methods of preparation |
| US7045618B2 (en) * | 2001-02-27 | 2006-05-16 | Ranbaxy Laboratories Limited | Cefpodixime proxetil |
| US20060293296A1 (en) * | 2002-12-20 | 2006-12-28 | Gharpure Milind M | Process for the preparation of cefpodoxime procetil |
| EP2520578A1 (en) | 2011-05-06 | 2012-11-07 | Lupin Limited | Process for purification of cephalosporins |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4203899A (en) * | 1974-12-19 | 1980-05-20 | Takeda Chemical Industries, Ltd. | Thiazolylacetamido compounds |
| US4668783A (en) * | 1974-12-19 | 1987-05-26 | Takeda Chemical Industries, Ltd. | Thiazolylacetamido cephalosporin compounds |
| US4298606A (en) * | 1974-12-19 | 1981-11-03 | Takeda Chemical Industries, Ltd. | Thiazolylacetamido compounds |
| JPS5760345B2 (cs) * | 1974-12-19 | 1982-12-18 | Takeda Chemical Industries Ltd | |
| DK154939C (da) * | 1974-12-19 | 1989-06-12 | Takeda Chemical Industries Ltd | Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf |
| DE2760123C2 (de) * | 1976-01-23 | 1986-04-30 | Roussel-Uclaf, Paris | 7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporansäuren, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen |
| JPS6011713B2 (ja) * | 1976-09-08 | 1985-03-27 | 武田薬品工業株式会社 | セフアロスポリン誘導体およびその製造法 |
| DE2714880A1 (de) * | 1977-04-02 | 1978-10-26 | Hoechst Ag | Cephemderivate und verfahren zu ihrer herstellung |
| US4409215A (en) * | 1979-11-19 | 1983-10-11 | Fujisawa Pharmaceutical Co., Ltd. | 7-Acylamino-3-substituted cephalosporanic acid derivatives and processes for the preparation thereof |
| FR2476087A1 (fr) * | 1980-02-18 | 1981-08-21 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-alkyloxy ou 3-alkyl-thiomethyl 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| JPS5759894A (en) * | 1980-09-30 | 1982-04-10 | Sankyo Co Ltd | Cephalosporin for oral administration |
| US4486425A (en) * | 1980-09-30 | 1984-12-04 | Sankyo Company Limited | 7-[2-(2-Aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylates |
| JPS5896091A (ja) * | 1981-12-01 | 1983-06-07 | Sankyo Co Ltd | ３−アルコキシメチルセフアロスポリン類の製造法 |
| US4688783A (en) * | 1983-04-20 | 1987-08-25 | Dubois R Clark | Bottom feed sheet feeding apparatus |
| JPS604189A (ja) * | 1983-06-20 | 1985-01-10 | Sankyo Co Ltd | β−ラクタム系化合物の製造法 |
| JPS604190A (ja) * | 1983-06-21 | 1985-01-10 | Sankyo Co Ltd | セフアロスポリン誘導体の製法 |
| JPS60260584A (ja) * | 1985-05-14 | 1985-12-23 | Sankyo Co Ltd | セフアロスポリン誘導体 |
| DE3804841A1 (de) * | 1988-02-17 | 1989-08-31 | Hoechst Ag | Cephalosporinderivate und verfahren zu ihrer herstellung |
| DE3901405A1 (de) * | 1989-01-19 | 1990-07-26 | Hoechst Ag | Cephalosporinderivate und verfahren zu ihrer herstellung |
| DE3910093A1 (de) * | 1989-03-29 | 1990-10-04 | Hoechst Ag | Cephalosporinderivate und verfahren zu ihrer herstellung |
| US5063224A (en) * | 1990-07-09 | 1991-11-05 | Eli Lilly And Company | R-cefuroxime axetil |
| ATE262533T1 (de) * | 1991-09-07 | 2004-04-15 | Aventis Pharma Gmbh | Diastereomer des 3-cephem-4-carbonsäure-1-(- isopropoxycarbonyloxy)ethylesters und verfahren zu dessen herstellung |
-
1992
- 1992-09-02 AT AT92114982T patent/ATE262533T1/de active
- 1992-09-02 DE DE59209994T patent/DE59209994D1/de not_active Expired - Lifetime
- 1992-09-02 PT PT92114982T patent/PT531875E/pt unknown
- 1992-09-02 ES ES92114982T patent/ES2215161T3/es not_active Expired - Lifetime
- 1992-09-02 DK DK92114982T patent/DK0531875T3/da active
- 1992-09-02 EP EP92114982A patent/EP0531875B1/de not_active Expired - Lifetime
- 1992-09-03 US US07/940,367 patent/US5461043A/en not_active Expired - Lifetime
- 1992-09-04 BR BR929203464A patent/BR9203464A/pt not_active Application Discontinuation
- 1992-09-04 HR HR920310A patent/HRP920310A2/hr not_active IP Right Cessation
- 1992-09-04 FI FI923966A patent/FI108725B/fi not_active IP Right Cessation
- 1992-09-04 RU SU925052750A patent/RU2075480C1/ru active
- 1992-09-04 SK SK2761-92A patent/SK279013B6/sk not_active IP Right Cessation
- 1992-09-04 PL PL92295834A patent/PL171644B1/pl unknown
- 1992-09-04 MX MX9205081A patent/MX9205081A/es unknown
- 1992-09-04 ZA ZA926710A patent/ZA926710B/xx unknown
- 1992-09-04 PH PH44890A patent/PH30743A/en unknown
- 1992-09-04 IL IL10306492A patent/IL103064A/en not_active IP Right Cessation
- 1992-09-04 NO NO923452A patent/NO302122B1/no not_active IP Right Cessation
- 1992-09-04 NZ NZ244224A patent/NZ244224A/en not_active IP Right Cessation
- 1992-09-04 RS YUP-813/92A patent/RS49877B/sr unknown
- 1992-09-04 CZ CS922761A patent/CZ282320B6/cs not_active IP Right Cessation
- 1992-09-04 CA CA002077562A patent/CA2077562C/en not_active Expired - Lifetime
- 1992-09-05 KR KR1019920016174A patent/KR100239253B1/ko not_active Expired - Lifetime
- 1992-09-05 EG EG52192A patent/EG20237A/xx active
- 1992-09-05 CN CN92110493A patent/CN1040002C/zh not_active Expired - Lifetime
- 1992-09-07 HU HU9202861A patent/HU219588B/hu unknown
- 1992-09-07 JP JP4280421A patent/JP2667943B2/ja not_active Expired - Lifetime
- 1992-09-07 SI SI9200204A patent/SI9200204B/sl unknown
- 1992-09-07 MA MA22936A patent/MA22646A1/fr unknown
- 1992-09-08 AU AU22183/92A patent/AU647307B2/en not_active Expired
-
1995
- 1995-05-22 US US08/447,229 patent/US5550232A/en not_active Expired - Lifetime
- 1995-05-22 US US08/447,249 patent/US5614623A/en not_active Expired - Lifetime
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